Sodium Iodide → HCID 59231977, compound

To a solution of 2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)ethanol (440 mg, 2.5 mmol) in THF (10 ml) and CH2Cl2 anhydrous (10 ml) and was added SOCl2 (0.36 ml, 4.9 mmol) and stirred at rt. After 20 min all starting material was consumed. The crude reaction mixture was concentrated in vacuo to dryness and was suspended in dry CH2Cl2. The solvent was evaporated and the crude was re-suspended in CH2Cl2 and concentrated in vacuo to dryness. The resulting solid was dissolved in DMF (10 ml) and was added triethylamine (0.97 ml, 7.2 mmol), morpholine (1.0 ml, 11.7 mmol) and NaI (280 mg, 1.87 mmol) and heated at 55° C. 24 h. Cooled to rt, the reaction crude was diluted with EtOAc (30 ml) and washed with H2O (2×) and brine (2×), dried over Na2SO4 and concentrated to give yellow solid. The crude was purified by MPLC with 0-10% MeOH/CH2Cl2 to give 149 mg of the titled compound (yield 25%). MS [M+H]+=248; LCMS RT=1.05 min.

1. customAfter 20 min all starting material was consumed
2. customThe crude reaction mixture
3. concentrationwas concentrated in vacuo to dryness
4. customThe solvent was evaporated
5. concentrationconcentrated in vacuo to dryness
6. dissolutionThe resulting solid was dissolved in DMF (10 ml)
7. temperatureheated at 55° C
8. custom24 h
9. temperatureCooled to rt
10. customthe reaction crude
11. washwashed with H2O (2×) and brine (2×)
12. dry with materialdried over Na2SO4
13. concentrationconcentrated
14. customto give yellow solid
15. customThe crude was purified by MPLC with 0-10% MeOH/CH2Cl2

ORD record

ord-4f97674947c749b784a138f8359035ab

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143393B2